Classic Cool Denim

GIF photographed by Alex Thebez. All others photographed by Jody Rogac.
Preppy gets a bad rap. But dig past the piles of critter-embroidered khakis and non-ironic headbands, and you'll find a chic undertone that’s applicable even if you’re not an Ivy Leaguer (and proud of it). There’s just something that feels a little transgressive about breaking up with novelty fashions for a more timeless aesthetic. The outfits ahead — complete with crisp collars and quirky loafers — show how any style of denim can leave its workwear roots to take on a sophisticated persona, but with a decidedly modern twist.
Fancy Footwork
Shoes are an easy starting place for non-preps to test the waters. Updated legacy styles, like T-strap Mary Janes and funked-up loafers, feel surprisingly unconventional. Slip 'em on sans socks, and show some ankle with cropped or cuffed jeans for that endless-summer vibe.
Left: Levi’s 311 Shaping Skinny Jeans (Plus), $69.50; Classic One Pocket Shirt, $68; Ribbed Pullover, $78. Dr. Martens shoes. Right: Levi’s 501 Jeans For Women, $79.90; Flight Bomber, $99.90. Stylist's own top, Pierre Hardy shoes.
Proper Collars
While the upper décolletage is a prep's landing surface for ropes of pearls and silk bow ties, it's also the backdrop for compelling collar details of all kinds. Two winners: the crisp white shirt collar (under a crewneck sweater, of course) and the sleeveless turtleneck. Instead of trousers, make the look modern with tailored, straight-leg jeans.
Left: Levi’s Classic One Pocket Shirt, $68; Ribbed Pullover, $78. Right: Levi’s 714 Straight Jeans, $78. Ji Oh top, Robert Clergerie shoes.
Retro Refined
Keep a prep-inspired look out of costume-y territory by tweaking the subculture's signatures to feel relevant. As in, don plaid in a forward-leaning dress shape and toned-down palette. Or use black jeans to bring an academic-style roll-neck and loafers into the here and now.
Left: Levi’s 714 Straight Jeans, $78. Ji Oh top, Robert Clergerie shoes. Right: Levi’s 711 Skinny Jeans, $78. Jenni Kayne dress, Jeffrey Campbell shoes.
Club Love
We can always get down with preppy varsity-inspired pieces that speak to our former collegiate selves (and our current athleisure addiction). Make like you're repping the club crew team with a logo-emblazoned sweatshirt, and swap workout leggings for body-hugging skinnies with a stretch that's just as forgiving.
Styling by Sue Choi; Hair by Andre Gunn at Honey Artists; Makeup by Grace Ahn; Nails by Casey Herman at Kate Ryan Inc.

More from Fashion

R29 Original Series